# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_16a
_database_code_depnum_ccdc_archive 'CCDC 1954308'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-01-29 downloaded from the CCDC.
;
_audit_creation_date             2019-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O4'
_chemical_formula_sum            'C9 H11 N O4'
_chemical_formula_weight         197.19
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2347(2)
_cell_length_b                   12.4282(2)
_cell_length_c                   20.6075(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1852.91(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    132629
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.86
_cell_measurement_theta_min      3.56
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.647
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  0.584
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0061
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            64018
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         73.415
_diffrn_reflns_theta_min         4.154
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3674
_reflns_number_total             3678
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.3573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C4B(H4BA,H4BB), C5B(H5BA,
 H5BB), C6B(H6BA,H6BB)
2.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.33043(17) 0.55250(9) 0.54246(5) 0.0250(3) Uani 1 1 d . . . . .
O2A O 0.39632(19) 0.66351(11) 0.45900(5) 0.0312(3) Uani 1 1 d . . . . .
O3A O 0.28281(18) 0.56286(9) 0.74776(5) 0.0262(3) Uani 1 1 d . . . . .
O4A O 0.21553(18) 0.38629(9) 0.74018(5) 0.0246(3) Uani 1 1 d . . . . .
N1A N 0.4398(2) 0.71599(11) 0.56557(6) 0.0206(3) Uani 1 1 d . . . . .
C1A C 0.3702(2) 0.67437(12) 0.62779(7) 0.0189(3) Uani 1 1 d . . . . .
H1A H 0.469090 0.674656 0.661694 0.023 Uiso 1 1 calc R . . . .
C2A C 0.3182(2) 0.56160(13) 0.60898(7) 0.0204(3) Uani 1 1 d . . . . .
C3A C 0.3918(2) 0.64981(13) 0.51638(8) 0.0227(3) Uani 1 1 d . . . . .
C4A C 0.4073(3) 0.83333(13) 0.55991(8) 0.0266(4) Uani 1 1 d . . . . .
H4AA H 0.337416 0.850463 0.519933 0.032 Uiso 1 1 calc R . . . .
H4AB H 0.525665 0.873337 0.559422 0.032 Uiso 1 1 calc R . . . .
C5A C 0.2935(3) 0.86097(12) 0.62096(8) 0.0249(3) Uani 1 1 d . . . . .
H5AA H 0.373040 0.894035 0.654592 0.030 Uiso 1 1 calc R . . . .
H5AB H 0.192435 0.911599 0.610200 0.030 Uiso 1 1 calc R . . . .
C6A C 0.2152(2) 0.75326(12) 0.64472(8) 0.0223(3) Uani 1 1 d . . . . .
H6AA H 0.191553 0.754678 0.692032 0.027 Uiso 1 1 calc R . . . .
H6AB H 0.099328 0.734763 0.621752 0.027 Uiso 1 1 calc R . . . .
C7A C 0.2680(2) 0.47672(12) 0.64430(8) 0.0219(3) Uani 1 1 d . . . . .
H7A H 0.238546 0.410967 0.623189 0.026 Uiso 1 1 calc R . . . .
C8A C 0.2575(2) 0.48318(12) 0.71524(8) 0.0207(3) Uani 1 1 d . . . . .
C9A C 0.2012(3) 0.38208(13) 0.80998(8) 0.0270(4) Uani 1 1 d . . . . .
H9AA H 0.092585 0.423048 0.824028 0.040 Uiso 1 1 calc GR . . . .
H9AB H 0.312621 0.413283 0.829389 0.040 Uiso 1 1 calc GR . . . .
H9AC H 0.188602 0.307045 0.823915 0.040 Uiso 1 1 calc GR . . . .
O1B O 0.26999(17) 0.05619(8) 0.48796(5) 0.0220(2) Uani 1 1 d . . . . .
O2B O 0.26866(18) 0.16987(10) 0.57389(5) 0.0268(3) Uani 1 1 d . . . . .
O3B O 0.2105(2) 0.06637(9) 0.28270(5) 0.0284(3) Uani 1 1 d . . . . .
O4B O 0.28473(18) -0.10954(9) 0.28656(5) 0.0248(3) Uani 1 1 d . . . . .
N1B N 0.16934(19) 0.22407(10) 0.47234(6) 0.0192(3) Uani 1 1 d . . . . .
C1B C 0.1913(2) 0.17972(12) 0.40654(7) 0.0194(3) Uani 1 1 d . . . . .
H1B H 0.071295 0.180979 0.382454 0.023 Uiso 1 1 calc R . . . .
C2B C 0.2488(2) 0.06597(12) 0.42179(7) 0.0197(3) Uani 1 1 d . . . . .
C3B C 0.2376(2) 0.15609(12) 0.51735(7) 0.0206(3) Uani 1 1 d . . . . .
C4B C 0.2177(2) 0.34002(12) 0.47454(8) 0.0226(3) Uani 1 1 d . . . . .
H4BA H 0.321429 0.353300 0.504827 0.027 Uiso 1 1 calc R . . . .
H4BB H 0.110252 0.384018 0.487995 0.027 Uiso 1 1 calc R . . . .
C5B C 0.2738(3) 0.36504(12) 0.40436(8) 0.0270(4) Uani 1 1 d . . . . .
H5BA H 0.378021 0.416645 0.403284 0.032 Uiso 1 1 calc R . . . .
H5BB H 0.168596 0.395967 0.379958 0.032 Uiso 1 1 calc R . . . .
C6B C 0.3316(3) 0.25632(12) 0.37545(8) 0.0239(3) Uani 1 1 d . . . . .
H6BA H 0.320872 0.256362 0.327555 0.029 Uiso 1 1 calc R . . . .
H6BB H 0.459788 0.237343 0.387797 0.029 Uiso 1 1 calc R . . . .
C7B C 0.2783(2) -0.01901(12) 0.38392(7) 0.0209(3) Uani 1 1 d . . . . .
H7B H 0.315918 -0.085112 0.402945 0.025 Uiso 1 1 calc R . . . .
C8B C 0.2540(2) -0.01258(12) 0.31322(7) 0.0210(3) Uani 1 1 d . . . . .
C9B C 0.2612(3) -0.11579(13) 0.21676(7) 0.0280(4) Uani 1 1 d . . . . .
H9BA H 0.349902 -0.067729 0.195523 0.042 Uiso 1 1 calc GR . . . .
H9BB H 0.135150 -0.093990 0.205310 0.042 Uiso 1 1 calc GR . . . .
H9BC H 0.282558 -0.189867 0.202299 0.042 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C2A 1.3783(18) . ?
O1A C3A 1.396(2) . ?
O2A C3A 1.195(2) . ?
O3A C8A 1.2098(19) . ?
O4A C8A 1.3440(18) . ?
O4A C9A 1.4431(19) . ?
N1A C1A 1.4715(19) . ?
N1A C3A 1.351(2) . ?
N1A C4A 1.482(2) . ?
C1A H1A 1.0000 . ?
C1A C2A 1.502(2) . ?
C1A C6A 1.530(2) . ?
C2A C7A 1.332(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.542(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.534(2) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.466(2) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
O1B C2B 1.3775(17) . ?
O1B C3B 1.4012(19) . ?
O2B C3B 1.1990(19) . ?
O3B C8B 1.207(2) . ?
O4B C8B 1.3430(19) . ?
O4B C9B 1.4504(18) . ?
N1B C1B 1.4722(19) . ?
N1B C3B 1.348(2) . ?
N1B C4B 1.4836(19) . ?
C1B H1B 1.0000 . ?
C1B C2B 1.507(2) . ?
C1B C6B 1.532(2) . ?
C2B C7B 1.331(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.534(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.535(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B H7B 0.9500 . ?
C7B C8B 1.470(2) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O1A C3A 109.40(12) . . ?
C8A O4A C9A 115.46(12) . . ?
C1A N1A C4A 111.12(12) . . ?
C3A N1A C1A 110.60(13) . . ?
C3A N1A C4A 119.97(13) . . ?
N1A C1A H1A 111.3 . . ?
N1A C1A C2A 100.88(12) . . ?
N1A C1A C6A 102.96(12) . . ?
C2A C1A H1A 111.3 . . ?
C2A C1A C6A 118.25(14) . . ?
C6A C1A H1A 111.3 . . ?
O1A C2A C1A 108.49(13) . . ?
C7A C2A O1A 119.73(14) . . ?
C7A C2A C1A 131.77(14) . . ?
O2A C3A O1A 120.87(15) . . ?
O2A C3A N1A 130.44(16) . . ?
N1A C3A O1A 108.70(13) . . ?
N1A C4A H4AA 111.0 . . ?
N1A C4A H4AB 111.0 . . ?
N1A C4A C5A 103.87(12) . . ?
H4AA C4A H4AB 109.0 . . ?
C5A C4A H4AA 111.0 . . ?
C5A C4A H4AB 111.0 . . ?
C4A C5A H5AA 110.7 . . ?
C4A C5A H5AB 110.7 . . ?
H5AA C5A H5AB 108.8 . . ?
C6A C5A C4A 105.26(12) . . ?
C6A C5A H5AA 110.7 . . ?
C6A C5A H5AB 110.7 . . ?
C1A C6A C5A 102.46(13) . . ?
C1A C6A H6AA 111.3 . . ?
C1A C6A H6AB 111.3 . . ?
C5A C6A H6AA 111.3 . . ?
C5A C6A H6AB 111.3 . . ?
H6AA C6A H6AB 109.2 . . ?
C2A C7A H7A 119.5 . . ?
C2A C7A C8A 121.04(14) . . ?
C8A C7A H7A 119.5 . . ?
O3A C8A O4A 123.76(14) . . ?
O3A C8A C7A 126.12(14) . . ?
O4A C8A C7A 110.12(13) . . ?
O4A C9A H9AA 109.5 . . ?
O4A C9A H9AB 109.5 . . ?
O4A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C2B O1B C3B 109.33(12) . . ?
C8B O4B C9B 115.74(12) . . ?
C1B N1B C4B 111.50(12) . . ?
C3B N1B C1B 111.07(12) . . ?
C3B N1B C4B 120.09(13) . . ?
N1B C1B H1B 111.0 . . ?
N1B C1B C2B 100.89(12) . . ?
N1B C1B C6B 102.94(12) . . ?
C2B C1B H1B 111.0 . . ?
C2B C1B C6B 119.15(14) . . ?
C6B C1B H1B 111.0 . . ?
O1B C2B C1B 108.66(12) . . ?
C7B C2B O1B 119.51(14) . . ?
C7B C2B C1B 131.82(14) . . ?
O2B C3B O1B 121.01(14) . . ?
O2B C3B N1B 130.38(15) . . ?
N1B C3B O1B 108.61(12) . . ?
N1B C4B H4BA 111.1 . . ?
N1B C4B H4BB 111.1 . . ?
N1B C4B C5B 103.33(12) . . ?
H4BA C4B H4BB 109.1 . . ?
C5B C4B H4BA 111.1 . . ?
C5B C4B H4BB 111.1 . . ?
C4B C5B H5BA 110.7 . . ?
C4B C5B H5BB 110.7 . . ?
C4B C5B C6B 105.05(12) . . ?
H5BA C5B H5BB 108.8 . . ?
C6B C5B H5BA 110.7 . . ?
C6B C5B H5BB 110.7 . . ?
C1B C6B C5B 101.77(13) . . ?
C1B C6B H6BA 111.4 . . ?
C1B C6B H6BB 111.4 . . ?
C5B C6B H6BA 111.4 . . ?
C5B C6B H6BB 111.4 . . ?
H6BA C6B H6BB 109.3 . . ?
C2B C7B H7B 119.4 . . ?
C2B C7B C8B 121.26(14) . . ?
C8B C7B H7B 119.4 . . ?
O3B C8B O4B 124.01(14) . . ?
O3B C8B C7B 126.30(14) . . ?
O4B C8B C7B 109.68(13) . . ?
O4B C9B H9BA 109.5 . . ?
O4B C9B H9BB 109.5 . . ?
O4B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20
_database_code_depnum_ccdc_archive 'CCDC 1954309'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-01-29 downloaded from the CCDC.
;
_audit_creation_date             2019-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N O4'
_chemical_formula_sum            'C8 H9 N O4'
_chemical_formula_weight         183.16
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.57010(10)
_cell_length_b                   7.7138(2)
_cell_length_c                   11.0161(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.4200(10)
_cell_angle_gamma                90
_cell_volume                     813.21(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    61898
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38003
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.502
_diffrn_reflns_theta_min         4.013
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3074
_reflns_number_total             3103
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.0064(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0223
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+0.1775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0579
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18999(15) -0.15463(19) 0.55905(13) 0.0297(3) Uani 1 1 d . . . . .
O2 O 0.39372(13) -0.05126(16) 0.63646(12) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.59425(13) 0.42797(16) 0.71219(12) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.78247(12) 0.26576(17) 0.75594(11) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.815420 0.362373 0.776610 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.21308(14) 0.1287(2) 0.62511(13) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.25331(19) -0.0338(3) 0.60101(16) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.10584(18) 0.2194(3) 0.55186(17) 0.0243(4) Uani 1 1 d . . . . .
H2A H 0.017250 0.230485 0.597041 0.029 Uiso 1 1 calc R . . . .
H2B H 0.087502 0.157692 0.474567 0.029 Uiso 1 1 calc R . . . .
C3 C 0.17201(19) 0.3977(3) 0.52903(17) 0.0226(4) Uani 1 1 d . . . . .
H3A H 0.135596 0.484609 0.586901 0.027 Uiso 1 1 calc R . . . .
H3B H 0.151834 0.437665 0.445308 0.027 Uiso 1 1 calc R . . . .
C4 C 0.33012(18) 0.3709(2) 0.54807(15) 0.0199(4) Uani 1 1 d . . . . .
H4A H 0.374416 0.322607 0.474514 0.024 Uiso 1 1 calc R . . . .
H4B H 0.377310 0.480600 0.570653 0.024 Uiso 1 1 calc R . . . .
C5 C 0.33303(16) 0.2409(2) 0.65276(15) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.319699 0.301444 0.732124 0.020 Uiso 1 1 calc R . . . .
C6 C 0.44831(18) 0.1093(2) 0.66240(15) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.58298(19) 0.1213(2) 0.69256(16) 0.0187(4) Uani 1 1 d . . . . .
H7 H 0.636941 0.018046 0.696506 0.022 Uiso 1 1 calc R . . . .
C8 C 0.65107(17) 0.2855(2) 0.71974(15) 0.0168(3) Uani 1 1 d . . . . .
O5 O 1.31063(13) 1.15226(17) 0.94351(12) 0.0221(3) Uani 1 1 d . . . . .
O6 O 1.09981(12) 1.04406(15) 0.88781(11) 0.0168(3) Uani 1 1 d . . . . .
O7 O 0.89842(13) 0.56237(16) 0.82226(11) 0.0190(3) Uani 1 1 d . . . . .
O8 O 0.72065(12) 0.72411(17) 0.75139(11) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.683383 0.626350 0.742174 0.032 Uiso 1 1 calc GR . . . .
N2 N 1.25551(14) 0.8622(2) 0.96791(12) 0.0163(3) Uani 1 1 d . . . . .
C9 C 1.23502(18) 1.0282(2) 0.93614(15) 0.0170(4) Uani 1 1 d . . . . .
C10 C 1.39275(16) 0.7751(3) 0.96023(16) 0.0203(4) Uani 1 1 d . . . . .
H10A H 1.440099 0.771630 1.040395 0.024 Uiso 1 1 calc R . . . .
H10B H 1.454232 0.833825 0.901189 0.024 Uiso 1 1 calc R . . . .
C11 C 1.35354(18) 0.5929(3) 0.91709(17) 0.0224(4) Uani 1 1 d . . . . .
H11A H 1.341011 0.513855 0.986973 0.027 Uiso 1 1 calc R . . . .
H11B H 1.426677 0.544981 0.863575 0.027 Uiso 1 1 calc R . . . .
C12 C 1.21560(17) 0.6166(2) 0.84718(16) 0.0201(4) Uani 1 1 d . . . . .
H12A H 1.231616 0.661495 0.764253 0.024 Uiso 1 1 calc R . . . .
H12B H 1.162387 0.506735 0.842153 0.024 Uiso 1 1 calc R . . . .
C13 C 1.14087(16) 0.7505(2) 0.92653(14) 0.0156(3) Uani 1 1 d . . . . .
H13 H 1.096570 0.691857 0.997492 0.019 Uiso 1 1 calc R . . . .
C14 C 1.04234(18) 0.8818(2) 0.87299(15) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.91589(19) 0.8701(2) 0.82196(15) 0.0179(3) Uani 1 1 d . . . . .
H15 H 0.869019 0.973769 0.799119 0.021 Uiso 1 1 calc R . . . .
C16 C 0.84683(17) 0.7049(2) 0.79988(14) 0.0165(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.202(2) . ?
O2 C1 1.403(2) . ?
O2 C6 1.374(2) . ?
O3 C8 1.229(2) . ?
O4 C8 1.325(2) . ?
N1 C1 1.339(3) . ?
N1 C2 1.477(2) . ?
N1 C5 1.468(2) . ?
C2 C3 1.536(3) . ?
C3 C4 1.540(2) . ?
C4 C5 1.528(2) . ?
C5 C6 1.503(2) . ?
C6 C7 1.332(3) . ?
C7 C8 1.454(2) . ?
O5 C9 1.202(2) . ?
O6 C9 1.401(2) . ?
O6 C14 1.377(2) . ?
O7 C16 1.230(2) . ?
O8 C16 1.325(2) . ?
N2 C9 1.342(2) . ?
N2 C10 1.478(2) . ?
N2 C13 1.465(2) . ?
C10 C11 1.529(3) . ?
C11 C12 1.534(2) . ?
C12 C13 1.533(2) . ?
C13 C14 1.502(2) . ?
C14 C15 1.334(2) . ?
C15 C16 1.455(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C1 109.48(14) . . ?
C1 N1 C2 122.33(15) . . ?
C1 N1 C5 111.58(14) . . ?
C5 N1 C2 111.93(15) . . ?
O1 C1 O2 120.79(17) . . ?
O1 C1 N1 131.10(17) . . ?
N1 C1 O2 108.10(15) . . ?
N1 C2 C3 103.17(14) . . ?
C2 C3 C4 105.26(14) . . ?
C5 C4 C3 101.74(13) . . ?
N1 C5 C4 102.73(13) . . ?
N1 C5 C6 100.89(14) . . ?
C6 C5 C4 120.39(14) . . ?
O2 C6 C5 108.47(14) . . ?
C7 C6 O2 118.71(16) . . ?
C7 C6 C5 132.80(17) . . ?
C6 C7 C8 122.89(16) . . ?
O3 C8 O4 122.78(15) . . ?
O3 C8 C7 124.58(15) . . ?
O4 C8 C7 112.64(14) . . ?
C14 O6 C9 109.44(13) . . ?
C9 N2 C10 123.17(15) . . ?
C9 N2 C13 111.88(14) . . ?
C13 N2 C10 112.23(14) . . ?
O5 C9 O6 120.66(16) . . ?
O5 C9 N2 130.96(17) . . ?
N2 C9 O6 108.38(14) . . ?
N2 C10 C11 102.67(13) . . ?
C10 C11 C12 104.76(14) . . ?
C13 C12 C11 101.38(13) . . ?
N2 C13 C12 102.84(13) . . ?
N2 C13 C14 101.07(14) . . ?
C14 C13 C12 121.64(14) . . ?
O6 C14 C13 108.52(14) . . ?
C15 C14 O6 118.17(16) . . ?
C15 C14 C13 133.24(17) . . ?
C14 C15 C16 122.64(17) . . ?
O7 C16 O8 122.96(16) . . ?
O7 C16 C15 124.64(15) . . ?
O8 C16 C15 112.41(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_21
_database_code_depnum_ccdc_archive 'CCDC 1954310'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2020-01-29 downloaded from the CCDC.
;
_audit_creation_date             2019-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H38 N2 O3'
_chemical_formula_sum            'C22 H38 N2 O3'
_chemical_formula_weight         378.54
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.52490(10)
_cell_length_b                   9.17550(10)
_cell_length_c                   24.7518(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.8450(10)
_cell_angle_gamma                90
_cell_volume                     2151.95(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    77628
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.25
_cell_measurement_theta_min      3.59
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.772
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68366
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.821
_diffrn_reflns_theta_min         3.590
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                7303
_reflns_number_total             7376
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2829 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7376
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.4065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C9A(H9AA,H9AB), C10A(H10A,
 H10B), C11A(H11A,H11B), C12A(H12A,H12B), C13A(H13A,H13B), C14A(H14A,H14B),
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,
 H19B), C20A(H20A,H20B), C21A(H21A,H21B), C4B(H4BA,H4BB), C5B(H5BA,H5BB),
 C6B(H6BA,H6BB), C9B(H9BA,H9BB), C10B(H10C,H10D), C11B(H11C,H11D), C12B(H12C,
 H12D), C13B(H13C,H13D), C14B(H14C,H14D), C15B(H15C,H15D), C16B(H16C,H16D),
 C17B(H17C,H17D), C18B(H18C,H18D), C19B(H19C,H19D), C20B(H20C,H20D), C21B(H21C,
 H21D)
2.c Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C7A(H7A), N2B(H2B), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C22A(H22A,H22B,H22C), C22B(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.74837(12) 0.24108(15) 0.08915(4) 0.0269(3) Uani 1 1 d . . . . .
O2A O 0.76683(14) 0.13634(17) 0.00729(5) 0.0355(3) Uani 1 1 d . . . . .
O3A O 1.00213(11) 0.46501(15) 0.21395(4) 0.0241(3) Uani 1 1 d . . . . .
N1A N 0.93018(15) 0.30440(19) 0.04436(5) 0.0267(3) Uani 1 1 d . . . . .
N2A N 0.79947(13) 0.52384(17) 0.24841(5) 0.0209(3) Uani 1 1 d . . . . .
H2A H 0.706983 0.515550 0.245812 0.025 Uiso 1 1 calc R . . . .
C1A C 0.96620(17) 0.3620(2) 0.09940(6) 0.0218(3) Uani 1 1 d . . . . .
H1A H 0.979601 0.469953 0.098159 0.026 Uiso 1 1 calc R . . . .
C2A C 0.83378(16) 0.32581(19) 0.12506(6) 0.0211(3) Uani 1 1 d . . . . .
C3A C 0.81515(19) 0.2199(2) 0.04194(6) 0.0275(4) Uani 1 1 d . . . . .
C4A C 1.05775(19) 0.2654(3) 0.01809(7) 0.0335(4) Uani 1 1 d . . . . .
H4AA H 1.066986 0.327078 -0.014184 0.040 Uiso 1 1 calc R . . . .
H4AB H 1.055896 0.161692 0.007063 0.040 Uiso 1 1 calc R . . . .
C5A C 1.17773(18) 0.2951(2) 0.06288(6) 0.0281(4) Uani 1 1 d . . . . .
H5AA H 1.219088 0.392826 0.058428 0.034 Uiso 1 1 calc R . . . .
H5AB H 1.253052 0.220937 0.062344 0.034 Uiso 1 1 calc R . . . .
C6A C 1.10717(16) 0.2864(2) 0.11598(6) 0.0236(3) Uani 1 1 d . . . . .
H6AA H 1.093433 0.184056 0.127019 0.028 Uiso 1 1 calc R . . . .
H6AB H 1.162668 0.338925 0.145881 0.028 Uiso 1 1 calc R . . . .
C7A C 0.78660(16) 0.3682(2) 0.17124(6) 0.0214(3) Uani 1 1 d . . . . .
H7A H 0.693876 0.340818 0.178103 0.026 Uiso 1 1 calc R . . . .
C8A C 0.87205(16) 0.45603(19) 0.21235(6) 0.0191(3) Uani 1 1 d . . . . .
C9A C 0.87121(16) 0.6111(2) 0.29188(7) 0.0204(3) Uani 1 1 d . . . . .
H9AA H 0.927944 0.687594 0.276093 0.024 Uiso 1 1 calc R . . . .
H9AB H 0.936321 0.548342 0.315333 0.024 Uiso 1 1 calc R . . . .
C10A C 0.76636(17) 0.6820(2) 0.32593(7) 0.0213(3) Uani 1 1 d . . . . .
H10A H 0.706079 0.605765 0.339961 0.026 Uiso 1 1 calc R . . . .
H10B H 0.704597 0.748748 0.302815 0.026 Uiso 1 1 calc R . . . .
C11A C 0.84048(17) 0.7673(2) 0.37358(7) 0.0211(3) Uani 1 1 d . . . . .
H11A H 0.902951 0.700251 0.396293 0.025 Uiso 1 1 calc R . . . .
H11B H 0.900537 0.843327 0.359312 0.025 Uiso 1 1 calc R . . . .
C12A C 0.73856(17) 0.8393(2) 0.40898(7) 0.0213(3) Uani 1 1 d . . . . .
H12A H 0.676102 0.763748 0.422114 0.026 Uiso 1 1 calc R . . . .
H12B H 0.678493 0.909102 0.386570 0.026 Uiso 1 1 calc R . . . .
C13A C 0.81256(17) 0.91999(19) 0.45781(7) 0.0207(3) Uani 1 1 d . . . . .
H13A H 0.872468 0.850245 0.480291 0.025 Uiso 1 1 calc R . . . .
H13B H 0.875118 0.995543 0.444710 0.025 Uiso 1 1 calc R . . . .
C14A C 0.71026(18) 0.9920(2) 0.49300(7) 0.0217(4) Uani 1 1 d . . . . .
H14A H 0.647252 0.916416 0.505765 0.026 Uiso 1 1 calc R . . . .
H14B H 0.650772 1.062029 0.470472 0.026 Uiso 1 1 calc R . . . .
C15A C 0.78251(17) 1.0723(2) 0.54223(7) 0.0213(3) Uani 1 1 d . . . . .
H15A H 0.842888 1.002783 0.564615 0.026 Uiso 1 1 calc R . . . .
H15B H 0.844456 1.149046 0.529536 0.026 Uiso 1 1 calc R . . . .
C16A C 0.67883(17) 1.1422(2) 0.57744(7) 0.0218(3) Uani 1 1 d . . . . .
H16A H 0.616770 1.065286 0.589934 0.026 Uiso 1 1 calc R . . . .
H16B H 0.618518 1.211536 0.554934 0.026 Uiso 1 1 calc R . . . .
C17A C 0.74898(17) 1.2228(2) 0.62692(6) 0.0212(3) Uani 1 1 d . . . . .
H17A H 0.808383 1.153364 0.649730 0.025 Uiso 1 1 calc R . . . .
H17B H 0.811753 1.299217 0.614531 0.025 Uiso 1 1 calc R . . . .
C18A C 0.64413(17) 1.2935(2) 0.66143(6) 0.0216(3) Uani 1 1 d . . . . .
H18A H 0.585040 1.216344 0.675551 0.026 Uiso 1 1 calc R . . . .
H18B H 0.581048 1.358473 0.638070 0.026 Uiso 1 1 calc R . . . .
C19A C 0.71356(17) 1.3816(2) 0.70915(6) 0.0207(3) Uani 1 1 d . . . . .
H19A H 0.774686 1.316169 0.733098 0.025 Uiso 1 1 calc R . . . .
H19B H 0.774462 1.457318 0.695176 0.025 Uiso 1 1 calc R . . . .
C20A C 0.60751(17) 1.4546(2) 0.74247(6) 0.0220(3) Uani 1 1 d . . . . .
H20A H 0.549616 1.378344 0.757770 0.026 Uiso 1 1 calc R . . . .
H20B H 0.543445 1.516081 0.718064 0.026 Uiso 1 1 calc R . . . .
C21A C 0.67497(17) 1.5491(2) 0.78886(6) 0.0221(4) Uani 1 1 d . . . . .
H21A H 0.735603 1.623445 0.773888 0.026 Uiso 1 1 calc R . . . .
H21B H 0.735961 1.487192 0.814240 0.026 Uiso 1 1 calc R . . . .
C22A C 0.56599(18) 1.6254(2) 0.82017(7) 0.0263(4) Uani 1 1 d . . . . .
H22A H 0.508776 1.691227 0.795726 0.039 Uiso 1 1 calc GR . . . .
H22B H 0.614478 1.681577 0.850169 0.039 Uiso 1 1 calc GR . . . .
H22C H 0.504771 1.552439 0.834697 0.039 Uiso 1 1 calc GR . . . .
O1B O 0.24296(12) 0.78548(15) 0.11042(4) 0.0257(3) Uani 1 1 d . . . . .
O2B O 0.26629(16) 0.95149(16) 0.04478(5) 0.0402(3) Uani 1 1 d . . . . .
O3B O 0.49995(11) 0.52074(15) 0.22131(4) 0.0246(3) Uani 1 1 d . . . . .
N1B N 0.46009(16) 0.83090(18) 0.08769(6) 0.0285(3) Uani 1 1 d . . . . .
N2B N 0.29859(13) 0.45400(16) 0.25567(5) 0.0190(3) Uani 1 1 d . . . . .
H2B H 0.205760 0.456820 0.252137 0.023 Uiso 1 1 calc R . . . .
C1B C 0.47642(17) 0.7039(2) 0.12358(6) 0.0229(3) Uani 1 1 d . . . . .
H1B H 0.549103 0.721606 0.154976 0.027 Uiso 1 1 calc R . . . .
C2B C 0.33109(17) 0.6925(2) 0.14179(6) 0.0208(3) Uani 1 1 d . . . . .
C3B C 0.3223(2) 0.8651(2) 0.07658(7) 0.0294(4) Uani 1 1 d . . . . .
C4B C 0.5548(2) 0.8191(2) 0.04364(7) 0.0380(5) Uani 1 1 d . . . . .
H4BA H 0.626646 0.897359 0.046617 0.046 Uiso 1 1 calc R . . . .
H4BB H 0.500271 0.824515 0.007437 0.046 Uiso 1 1 calc R . . . .
C5B C 0.6236(2) 0.6691(2) 0.05294(7) 0.0343(5) Uani 1 1 d . . . . .
H5BA H 0.718322 0.678124 0.073216 0.041 Uiso 1 1 calc R . . . .
H5BB H 0.633033 0.619722 0.017921 0.041 Uiso 1 1 calc R . . . .
C6B C 0.52338(18) 0.5844(2) 0.08621(6) 0.0251(4) Uani 1 1 d . . . . .
H6BA H 0.442408 0.543732 0.062746 0.030 Uiso 1 1 calc R . . . .
H6BB H 0.573027 0.504553 0.107194 0.030 Uiso 1 1 calc R . . . .
C7B C 0.27979(16) 0.61425(19) 0.18037(6) 0.0201(3) Uani 1 1 d . . . . .
H7B H 0.180831 0.615226 0.182639 0.024 Uiso 1 1 calc R . . . .
C8B C 0.36940(16) 0.52602(19) 0.21981(6) 0.0189(3) Uani 1 1 d . . . . .
C9B C 0.37150(16) 0.3713(2) 0.30028(6) 0.0203(3) Uani 1 1 d . . . . .
H9BA H 0.435216 0.436904 0.323106 0.024 Uiso 1 1 calc R . . . .
H9BB H 0.429755 0.294442 0.285512 0.024 Uiso 1 1 calc R . . . .
C10B C 0.26718(16) 0.3018(2) 0.33480(6) 0.0197(3) Uani 1 1 d . . . . .
H10C H 0.204943 0.234874 0.311967 0.024 Uiso 1 1 calc R . . . .
H10D H 0.207282 0.378821 0.348569 0.024 Uiso 1 1 calc R . . . .
C11B C 0.34035(17) 0.2172(2) 0.38284(6) 0.0210(3) Uani 1 1 d . . . . .
H11C H 0.400572 0.140700 0.368946 0.025 Uiso 1 1 calc R . . . .
H11D H 0.402545 0.284436 0.405567 0.025 Uiso 1 1 calc R . . . .
C12B C 0.23750(17) 0.1461(2) 0.41803(6) 0.0203(3) Uani 1 1 d . . . . .
H12C H 0.176833 0.077213 0.395465 0.024 Uiso 1 1 calc R . . . .
H12D H 0.175723 0.222402 0.431142 0.024 Uiso 1 1 calc R . . . .
C13B C 0.30980(17) 0.0644(2) 0.46686(7) 0.0212(3) Uani 1 1 d . . . . .
H13C H 0.371910 -0.011640 0.453792 0.025 Uiso 1 1 calc R . . . .
H13D H 0.370060 0.133358 0.489563 0.025 Uiso 1 1 calc R . . . .
C14B C 0.20653(17) -0.0070(2) 0.50172(7) 0.0209(3) Uani 1 1 d . . . . .
H14C H 0.146552 -0.076080 0.478947 0.025 Uiso 1 1 calc R . . . .
H14D H 0.144116 0.069114 0.514518 0.025 Uiso 1 1 calc R . . . .
C15B C 0.27721(18) -0.0888(2) 0.55094(7) 0.0216(3) Uani 1 1 d . . . . .
H15C H 0.338942 -0.165646 0.538214 0.026 Uiso 1 1 calc R . . . .
H15D H 0.337677 -0.020042 0.573669 0.026 Uiso 1 1 calc R . . . .
C16B C 0.17228(17) -0.1588(2) 0.58571(7) 0.0210(3) Uani 1 1 d . . . . .
H16C H 0.112100 -0.227695 0.562960 0.025 Uiso 1 1 calc R . . . .
H16D H 0.110239 -0.081854 0.598215 0.025 Uiso 1 1 calc R . . . .
C17B C 0.24197(17) -0.2403(2) 0.63522(7) 0.0216(4) Uani 1 1 d . . . . .
H17C H 0.304116 -0.317064 0.622716 0.026 Uiso 1 1 calc R . . . .
H17D H 0.302049 -0.171282 0.657993 0.026 Uiso 1 1 calc R . . . .
C18B C 0.13727(17) -0.3103(2) 0.66989(7) 0.0212(3) Uani 1 1 d . . . . .
H18C H 0.075051 -0.376949 0.646920 0.025 Uiso 1 1 calc R . . . .
H18D H 0.077311 -0.233224 0.683568 0.025 Uiso 1 1 calc R . . . .
C19B C 0.20860(17) -0.3955(2) 0.71808(6) 0.0214(4) Uani 1 1 d . . . . .
H19C H 0.267587 -0.473193 0.704250 0.026 Uiso 1 1 calc R . . . .
H19D H 0.272053 -0.328973 0.740605 0.026 Uiso 1 1 calc R . . . .
C20B C 0.10560(17) -0.4648(2) 0.75385(7) 0.0229(4) Uani 1 1 d . . . . .
H20C H 0.042183 -0.531582 0.731439 0.028 Uiso 1 1 calc R . . . .
H20D H 0.046627 -0.387267 0.767807 0.028 Uiso 1 1 calc R . . . .
C21B C 0.17877(18) -0.5496(2) 0.80186(7) 0.0267(4) Uani 1 1 d . . . . .
H21C H 0.241320 -0.623979 0.788021 0.032 Uiso 1 1 calc R . . . .
H21D H 0.238589 -0.481768 0.825270 0.032 Uiso 1 1 calc R . . . .
C22B C 0.0757(2) -0.6246(2) 0.83595(8) 0.0346(4) Uani 1 1 d . . . . .
H22D H 0.018606 -0.694780 0.813408 0.052 Uiso 1 1 calc GR . . . .
H22E H 0.013807 -0.551504 0.850043 0.052 Uiso 1 1 calc GR . . . .
H22F H 0.128335 -0.675666 0.866345 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C2A 1.3817(19) . ?
O1A C3A 1.400(2) . ?
O2A C3A 1.206(2) . ?
O3A C8A 1.2384(19) . ?
N1A C1A 1.4688(19) . ?
N1A C3A 1.339(2) . ?
N1A C4A 1.479(2) . ?
N2A C8A 1.337(2) . ?
N2A C9A 1.455(2) . ?
C1A C2A 1.506(2) . ?
C1A C6A 1.530(2) . ?
C2A C7A 1.328(2) . ?
C4A C5A 1.533(2) . ?
C5A C6A 1.538(2) . ?
C7A C8A 1.476(2) . ?
C9A C10A 1.517(2) . ?
C10A C11A 1.527(2) . ?
C11A C12A 1.524(2) . ?
C12A C13A 1.527(2) . ?
C13A C14A 1.523(2) . ?
C14A C15A 1.527(2) . ?
C15A C16A 1.523(2) . ?
C16A C17A 1.526(2) . ?
C17A C18A 1.523(2) . ?
C18A C19A 1.525(2) . ?
C19A C20A 1.523(2) . ?
C20A C21A 1.527(2) . ?
C21A C22A 1.527(2) . ?
O1B C2B 1.379(2) . ?
O1B C3B 1.391(2) . ?
O2B C3B 1.203(2) . ?
O3B C8B 1.2412(19) . ?
N1B C1B 1.464(2) . ?
N1B C3B 1.350(2) . ?
N1B C4B 1.488(2) . ?
N2B C8B 1.342(2) . ?
N2B C9B 1.4565(19) . ?
C1B C2B 1.502(2) . ?
C1B C6B 1.530(2) . ?
C2B C7B 1.327(2) . ?
C4B C5B 1.532(3) . ?
C5B C6B 1.534(2) . ?
C7B C8B 1.472(2) . ?
C9B C10B 1.515(2) . ?
C10B C11B 1.528(2) . ?
C11B C12B 1.522(2) . ?
C12B C13B 1.526(2) . ?
C13B C14B 1.521(2) . ?
C14B C15B 1.527(2) . ?
C15B C16B 1.526(2) . ?
C16B C17B 1.528(2) . ?
C17B C18B 1.523(2) . ?
C18B C19B 1.527(2) . ?
C19B C20B 1.526(2) . ?
C20B C21B 1.528(2) . ?
C21B C22B 1.522(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O1A C3A 109.11(13) . . ?
C1A N1A C4A 111.71(13) . . ?
C3A N1A C1A 111.26(13) . . ?
C3A N1A C4A 123.07(16) . . ?
C8A N2A C9A 120.94(13) . . ?
N1A C1A C2A 100.69(13) . . ?
N1A C1A C6A 101.62(13) . . ?
C2A C1A C6A 122.48(14) . . ?
O1A C2A C1A 108.43(13) . . ?
C7A C2A O1A 119.32(14) . . ?
C7A C2A C1A 132.05(15) . . ?
O2A C3A O1A 120.59(16) . . ?
O2A C3A N1A 130.64(17) . . ?
N1A C3A O1A 108.77(14) . . ?
N1A C4A C5A 102.96(13) . . ?
C4A C5A C6A 104.50(13) . . ?
C1A C6A C5A 101.25(13) . . ?
C2A C7A C8A 122.81(14) . . ?
O3A C8A N2A 122.10(14) . . ?
O3A C8A C7A 122.55(15) . . ?
N2A C8A C7A 115.34(13) . . ?
N2A C9A C10A 111.14(12) . . ?
C9A C10A C11A 111.71(13) . . ?
C12A C11A C10A 113.27(13) . . ?
C11A C12A C13A 113.32(13) . . ?
C14A C13A C12A 113.11(13) . . ?
C13A C14A C15A 113.80(13) . . ?
C16A C15A C14A 113.19(13) . . ?
C15A C16A C17A 114.01(13) . . ?
C18A C17A C16A 113.45(13) . . ?
C17A C18A C19A 113.73(13) . . ?
C20A C19A C18A 113.17(13) . . ?
C19A C20A C21A 113.92(13) . . ?
C20A C21A C22A 112.71(14) . . ?
C2B O1B C3B 109.10(13) . . ?
C1B N1B C4B 110.59(15) . . ?
C3B N1B C1B 110.45(14) . . ?
C3B N1B C4B 121.12(15) . . ?
C8B N2B C9B 121.67(12) . . ?
N1B C1B C2B 101.15(14) . . ?
N1B C1B C6B 102.88(12) . . ?
C2B C1B C6B 117.80(14) . . ?
O1B C2B C1B 108.33(13) . . ?
C7B C2B O1B 119.48(14) . . ?
C7B C2B C1B 132.19(15) . . ?
O2B C3B O1B 120.55(18) . . ?
O2B C3B N1B 130.04(18) . . ?
N1B C3B O1B 109.37(14) . . ?
N1B C4B C5B 103.75(15) . . ?
C4B C5B C6B 104.79(15) . . ?
C1B C6B C5B 101.41(15) . . ?
C2B C7B C8B 122.92(14) . . ?
O3B C8B N2B 122.03(15) . . ?
O3B C8B C7B 123.56(15) . . ?
N2B C8B C7B 114.38(13) . . ?
N2B C9B C10B 110.93(12) . . ?
C9B C10B C11B 112.29(13) . . ?
C12B C11B C10B 113.20(13) . . ?
C11B C12B C13B 113.51(13) . . ?
C14B C13B C12B 113.28(13) . . ?
C13B C14B C15B 113.96(13) . . ?
C16B C15B C14B 113.32(13) . . ?
C15B C16B C17B 113.72(13) . . ?
C18B C17B C16B 113.74(13) . . ?
C17B C18B C19B 113.06(13) . . ?
C20B C19B C18B 113.92(13) . . ?
C19B C20B C21B 113.22(13) . . ?
C22B C21B C20B 113.10(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
